Hydrogen cyanide, from oxidation amines

Precaution DOT Corrosive material combustible exposed to heat or flame can react with oxidizers ignites on contact with cellulose nitrate (high surf, area) may absorb CO2 from air to form carbamate salts Hazardous Decomp. Prods. CO, CO2, hydrogen cyanide, ammonia, volatile amines, irritating aldehydes and ketones heated to decomp., emits toxic fumes of NOx NFPA Health 3, Flammability 1, Reactivity 0 Storage Hygroscopic... 

Tricyanovinyl-N,N-dimethylaniline has been prepared by adding hydrogen cyanide to -dimethylaminobenzalmalono-nitrile and oxidizing the adduct.3 The present procedure, an adaptation of one that has been published,3 is the more convenient preparative method. It can be applied to a wide variety of secondary and tertiary aromatic amines to give />-tricyanovinyl-arylamines that, like the present one, are dyes.3 Other types of aromatic compounds also condense with tetracyanoethylene in this manner. Thus one can obtain 4-tricyano vinyl-2,6-dimethyl-phenol from 2,6-dimethylphenol, 2-tricyanovinylpyrrole from pyrrole, and 9-tricyanovinylphenanthrene from phenanthrene.4... 

In oxidation reactions, however, osmium is significantly more selective than catalysts derived from other transition metals. Osmium-based catalysts for the hydroxylation and amination of aUcenes are very widely used in organic synthesis. With alkaloid-derived ligands, the hydroxylation and amination reactions are highly enantioselective (see Enantioselectivity). The use of bleach, hydrogen peroxide, ferric cyanide, and oxygen have been reported as secondary oxidants for some of these reactions. 

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